


Seasons Come and Seasons Go, But You're Always By My Side

by LightLeadingMe



Category: Will & Grace
Genre: Best Friends, Cuddling & Snuggling, F/M, Fluff, Friendship, Gen, Platonic Cuddling
Language: English
Status: Completed
Published: 2018-11-16
Updated: 2018-11-16
Packaged: 2019-08-24 06:52:05
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 4,490
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16635017
Author URL: https://archiveofourown.org/users/LightLeadingMe/pseuds/LightLeadingMe
Summary: (or Five Times Jack and Karen Were Caught Being Innocent and the One Time They Weren't)





	Seasons Come and Seasons Go, But You're Always By My Side

**Author's Note:**

> I obviously love Jack and Karen snuggles.

_August 2000_

Rosario grumbled under her breath as she entered the bedroom, taking in the disarray of empty bottles and general haphazardness of items that littered the floor. She wasn't sure what time the foursome arrived at the manse, but she knew it was way into the early hours of the morning. She had received a drunken call from her boss the night before, the loud background music from the club making it hard for the woman to hear. The maid had rolled her eyes as she listened to the slurring demands and ended up hanging up on Karen, knowing the woman would black out eventually and forget about the entire phone conversation.  
  
As she stalked into the room, picking up various items, she noticed four lumps on the large bed and smirked. Will was at the very end, laying sideways, his leg dangling off the bed, shoe covered foot toeing the floor. Just above him, with her foot on her roommate's chest was Grace, completely star-fished out and taking up as much room as she could. Near the top of the bed on the right side was Karen, lying on her back, one arm over the side of the bed, hand on the nightstand where a beer bottle was knocked over and most likely spilled on the white carpet. Curled into her side was Jack, his head on her chest, face practically buried in the material of her blouse that had ridden up a bit over her stomach. His arm was draped over her waist tightly like he was hugging her to him, one of his legs between hers, hooked around her thigh. Karen's other hand was cupping Jack's jaw, her thumb on his cheek and if Rosie didn't know any better, she would guess that the socialite fell asleep caressing the young man's face.  
  
She smiled at the sweet sight. Her boss talked a lot of smack about her friends most of the time, but Rosie knew deep down that she loved them dearly. It took the crass woman forever to let these people in, always pushing them away when she feared they were getting too close, but it seemed that in the past year or so that she finally accepted that these three very different people were making a positive difference in her life, so she finally accepted them in... to an extent, of course. And she especially took an immediate liking to Jack, doting on him any chance she could get. They had such a strange relationship and while many others questioned or judged, the maid always found the unconventiality of it refreshing. A lot of times it was inappropriate, but mostly it was nice to know that her boss and friend had someone who could make her laugh like no one else and who adored her just as much as she adored him.  
  
Deciding the room could go a little bit longer without being tidied up, Rosario turned around and quietly exited, glancing back over her shoulder at the fabulous foursome, her prescense going completely unnoticed.

* * *

_September 2001_

Will knocked lightly on Jack's apartment door before entering quietly, cautious of his footsteps in case he was sleeping. His friend had come into his office earlier that afternoon, hysterically crying over a man that had dumped him. Will usually waved off the situation considering Jack had a different boyfriend every week, but this time it was different. Jack and this guy had been dating for almost two months and he had never seen his friend so happy. Will didn't have time to comfort Jack when he barged through his office door seeing as he was with a client and the whole thing was making him look bad. He guided the devastated man out to the hallway as he profusely apologized to his client and then told Jack to go home and calm down and that he would be by later so they could talk everything out. 

It was now 7pm, Will only getting home from work twenty minutes ago. He changed into a pair of sweatpants and threw on a tshirt before striding across the hall to 9A. As he crept through the apartment he squinted his eyes in the dark, trying to navigate his way to the bedroom where he assumed Jack was for the night. He turned the doorknob slowly and pushed the door open, peering inside. A smile broke out onto Will's face at the sight before him. Of course she would be there. If Will was unable to be at Jack's beck and call then Karen would come to the rescue. Sometimes they would conquer Jack's issues together as a team, a joint effort. He never understood Jack and Karen's relationship, but he knew he could never judge considering his and Grace's relationship was just as if not more dysfunctional.  
  
He leaned against the doorway and crossed his arms over his chest, taking in the sweet sight of his two friends. The sheets were at their waists, their legs tangled beneath. Karen was behind Jack, her chest against his bare back and her nose in the crook of his neck, her lips pressed to the skin of his shoulder. Her arm was draped over his waist and Jack's hand was holding hers across his stomach. Their even and steady breaths were deep, both friends in a comfortable slumber. Will frowned slightly at the dried tear stains on Jack's face, but ultimately he knew that his friend was being taken care of by Karen. He slowly backed out of the door and headed over to his own apartment.  
  
Grace was on the couch reading a magazine when he entered and looked up at him. "You weren't over there long," she said in confusion. "Is he okay?"  
  
Will smiled and sat beside her, taking the magazine from her lap and patting her knee. "He'll be fine. Karen is with him now."  
  
Graced caught his eye and nodded at him in understanding before laying her head on his shoulder as Will turned the page and they read together in silence.

* * *

_October 2001_

Stan returned home later than expected from his business trip, the warmth of the foyer a welcoming contrast to the cold air locked behind the door he just entered. He took off his coat and hung it on the coat rack beside his wife's, smiling as he noted Olivia and Mason's own fall wear on the lower rung. Usually Stan had to pick up his kids from their mother on his way home from the airport, but was told by Rosario when he called this morning that Karen had already collected them yesterday. It wasn't as surprising to him as it was to the maid - Karen let her guard down around her husband way more than she did around the El Salvadorian woman, no matter how close they were. She had a soft spot for her stepchildren and it made Stan love her all the more.  
  
He ascended the steps to the third floor and turned down the hall to the right, hearing voices as he neared his bedroom door. A squeal and a giggle that was unmistakeably Karen made Stan's eyebrows raise in curiosity. He slowly pushed open the door and peered inside to see Karen lying upside down on the bed, her best friend lying correctly right beside her, their heads together and resting on each other's shoulders. He could see Karen's box of photographs on the floor at the end of the bed, a few stray photos littering the sheets. The pair were giggling as they looked at a photo that Jack held in the air over their faces, Karen pointing to the image and telling a story. He couldn't quite make out what they were saying due to the distance between the door and the bed, but he continued to watch on silently. As Jack spoke, his wife turned her head to gaze lovingly at the blue-eyed man and when he was done talking, Jack looked over just in time for Karen to capture his bottom lip between hers in soft kiss.  
  
Stan knew the innocence behind the kiss, his wife and her best friend were many times overtly affectionate. Quite often he found them cuddling together or sharing small touches and kisses when the gay man lived in their home during the time he was married to Rosario. He was never jealous of Jack, if anything he was grateful that Karen had someone to spend her free time with while he was away on business or working for days on end. He cleared his throat as he fully entered the room, smirking when Karen shot up with a startled shriek.  
  
"Stanley!" she exclaimed as she scrambled off the bed to greet him. "I expected you back hours ago."  
  
He sighed as he placed his hands on her hips, feeling the silky material of her black nightgown beneath his fingertips. "I know, sweetie. I had a last minute meeting and had to transfer flights. But I'm home now." He leaned down and kissed her pouty lips, smiling into her when he noticed her standing on her tip toes to reach him. Pulling away, he looked up from his beaming wife's beautiful face. "Jack," he addressed the man who now stood slightly awkwardly beside the bed.  
  
"Hi, Mr. Walker," Jack said as he waved. "How was your trip?"  
  
"Long and boring." He looked down at his wife who was still in his arms. "Was this one any trouble?"  
  
Jack scoffed in an obvious manner and stepped down from the platform the bed was on. "She's always trouble," he said. Karen giggled, snuggling further into her husband's arms. Jack began to step towards the bedroom door after donning his shoes. "Well, I'll see you tomorrow, Kare."  
  
"Wait, Jackie," Karen spoke up, stopping his movements. "I'll walk you out." She looked up at Stan with a sly grin, a devious gleam in her eye. "You go take a shower and meet me in that bed in five minutes."  
  
Stan felt his face heat up as a blush rose to his cheeks. "I'll be here," he assured her with a pat on her ass. Karen winked and then rushed over to Jack who was waiting by the door. He watched their hands immediately reach for each other and heard their mindless chatter as they exited the room. Shaking his head, Stanley turned to enter the bathroom, throwing his tie on the floor as he went, his heart beating rapidly in anticipation for his wife's return.

* * *

_November 2003_

"Thank you, Paul. I had a great time," Grace said with a smile to the man who just returned her home from their date. Her hand was on the door knob of her apartment, her back facing the 9C as she gazed up at the taller gentleman who grinned back. 

"Yeah. I did, too, Grace," Paul replied with a nervous shuffle of his feet. He lifted his hand and scratched the back of his neck. "Well, uh, I'll call you." He hesitated at first, but then finally leaned down and kissed the redhead's cheek with a blush creeping up his neck.  
  
Grace's grin was wide and bright, her own cheeks warm and her stomach fluttering. "Goodnight," she whispered as the man turned towards the elevators. She bit her lip and spun around to unlock the door. It was later in the evening, Will was probably in bed already, so Grace crept in slowly, trying to make as little noise as possible. The apartment was dark, but a blue light was being cast from the couch in front of the TV. Frowning, Grace walked over to the area and raised her eyebrows at the sight she was greeted with. Karen was laying on the couch, her back resting against the armrest, her knees slightly bent and legs over Jack's lap with her head pressed into the cushions at the back of the couch. Jack was laying against her sideways, his face nestled in her breasts and his arm draped over her stomach, hanging slightly off the couch. Karen's arms were cradling his head sweetly, her nails gently scraping along his scalp by his ear. Grace noticed their eyes were sleepy, but open as they watched the television.  
  
"Uhh, Jack? Karen?" she asked softly to get their attention.  
  
Neither moved, but Karen did turn her eyes to the woman to smile at her. "Hey, Gracie," she mumbled. "Your husband is in bed already."  
  
Rolling her eyes, Grace began to take off her scarf and coat, setting them on the chair behind her. "Will is not my husband."  
  
"Might as well be," Jack mumbled.  
  
With a sigh, Grace stepped up to the kitchen to grab a water bottle. "What are you guys doing here anyway? Does Will even know you're here?"  
  
"My Jackie had a rough day," Karen replied, her finger now gently tracing his ear. "We needed a night of sappy movies and cuddling."  
  
Grace narrowed her eyes after taking a sip of water. "And you couldn't do that at your own apartments?"  
  
"Oh my God. Stop with the third degree, Dad," Jack grumbled, snuggling his face more into Karen's bosom.  
  
The redhead glared and was about to retort when a pleading look from Karen stopped her. Grace clamped her mouth shut, a slight pout on her lips and surprise evident in her eyes. She didn't know what happened to upset Jack so much, but it must have been something pretty bad to warrant a silent plea from Karen to not provoke the man. She nodded slowly at the brunette and cleared her throat. "Well, I'm going to bed. Lock up when you guys leave, please."  
  
Karen smiled in gratitude at the woman and looked back down at the man in her arms, whispering something in his ear. Grace kept her eyes on them as she began to walk away, catching a glimpse of Jack hugging her tighter to him and Karen pressing her lips to his hair.  
  
The next morning, Grace woke up to her stomach growling and she trudged out of bed, shuffling her feet across the hardwood floor towards the kitchen. She passed the small TV cove and took one step up to the kitchen, but then paused halfway. Turning her head she peered into the room to see Jack and Karen in the exact same position they were in last night, sound asleep with a blanket draped over their bodies. A door opened behind her and Grace glanced over to see Will walking out of the bathroom in his pajamas. She pointed to the sofa and Will nodded knowingly as he made his way over to her.  
  
"Found 'em a few minutes ago," he told her.  
  
"When I came home last night they were watching TV like that," Grace commented as she walked into the kitchen, Will trailing behind. "Karen said Jack had a bad day. I tried to ask more questions, but Jack got defensive."  
  
"You know it's funny," Will said with a smile as he grabbed some bowls from the cabinet. "They make fun of us constantly about our relationship, but sometimes I think they rely on each other just as much as we do."  
  
Grace nodded, opening the fridge to grab some milk. "They're freakin' weirdos, no doubt, but you're right."  
  
They grabbed the rest of their breakfast items and made their way to the table, sitting down to eat. Every few minutes, the pair at the table would glance behind them during their meal as they chatted lightly to look at the sweet sight of their friends, small smiles playing at their lips.

* * *

_December 2003_

"Rosie!"  
  
The El Salvadorian woman rolled her eyes heavenward at the bark from her boss. She flipped off her Telenovela and stood up, wincing at her aching back muscles. Pushing open the the swinging kitchen door, the maid walked down the hall towards the sound of chatting in the entryway. As she entered the room she saw Jack and Karen brushing snow off of each other, their cheeks and noses red from the harsh air of winter. "Getting in the Christmas spirit?" she quipped.  
  
"Christmas spirit," Karen scoffed as she threw her coat on the floor, tossing her wet gloves on top of it. "This dumbass over here thought it would be fun to build a snowman during a fucking blizzard." She pointed to Jack who was also removing his wet clothes, a glare in her eyes as she spoke.  
  
Jack gawked. "Like you didn't have fun? You almost peed yourself from laughing when those kids went crying to their mom because you kept pummeling them with snowballs!"  
  
Karen squinted her eyes in thought before a grin broke out onto her face. "Okay, that was fun." She looked over at Rosario and snapped her fingers rudely at the woman. "We want some hot chocolate and Baileys, senorita. We'll be in the lounge by the fireplace."  
  
"Listen, lady," the maid started in. "You can't just snap your fingers and expect me to-"  
  
"Now you listen-" Karen began and the two women erupted into a pointless argument, each voice rising higher over the other. After a full minute they finally stopped, their last words echoing in the foyer as they glared at each other. Finally, Karen winked at her friend, a grin spreading over her face. "Aww, RoRo, you're the best." She puckered her lips and the woman bent over to peck her mouth.  
  
"You two go get warmed up," the older woman said. "I'll be up in a minute." She turned and hurried to the kitchen to begin making their cocoa. She opened the pantry for some cookies, placing them along with two mugs on a festive holiday serving tray. When the cocoa was done, she poured the steaming liquid into the mugs, putting some Bailey's in Karen's and extra marshmallows in Jack's. She carefully made her way up to the lounge and she sighed in exasperation when she saw the door to the room was closed. Setting the tray down on the floor of the hall, Rosario turned the knob and opened the door to step in, but stopped short when she saw the position of her boss and her ex-husband.  
  
They were on the large chair in front of the lit up fireplace all snuggled together. Karen had her legs on either side of Jack's hips, straddling him, her nose in his neck. Jack's hands were rubbing up and down her back slowly, fingers tickling over the soft material of her cashmere sweater.  
  
"I'm still cold, Jackie," she heard the brunette mumble. "My ass is like an icicle."  
  
Jack giggled and slid his fingers down her back. "Well, I can fix that." His hands disappeared beneath the waistband of her pants, cupping her butt cheeks as she snickered and kissed his neck.  
  
Rosario picked up the tray and cleared her throat as she entered the room. "Hot chocolate for Boozo and her Clown," she announced, setting the tray on the table beside the chair. She was slightly surprised when neither of them moved for the warm beverage.  
  
"Thanks Rosie," Jack beamed at her appreciatively.  
  
Rosario shook her head, eyeing them still. "You two really have no boundaries, do you?"  
  
Karen's head snapped up to badger the maid, but Jack quickly distracted her by pinching her bare ass, causing the small woman to squeal in laughter. "Jackie!" she jokingly smacked his chest in a playful manner. "Don't make me tickle you!"  
  
Rosario chose that moment to exit the room, not wanting to be around when their playing around turned way more inappropriate than what she just witnessed. Over the years, the friendship between the wealthy woman and the gay man seemed to have developed way different than what Rosario expected. Jack and Karen had the strangest relationship in her eyes, always dancing around the border of highly improper and very dysfunctional. She questioned many times how far they actually went before they realized it was too far. Jack's sexuality seemed to almost always waiver when it came to Karen, something the maid wondered if the two even realized. The door clicked behind her just as the squeals of laughter kicked up a notch on the other side and Rosario quickly went down the hallway to the stairwell, hoping she could still catch the rest of her TV program before it ended.

* * *

_January 2004_

Will sipped from his champagne flute, his shoulder leaning against the doorway as his eyes scanned the room of people he didn't know. Of the seven years he knew Karen Walker, he had never been invited to a Christmas dinner at her large home. She only invited a few people, mostly other socialites that she hated, but she needed to keep up her status as the widow of Stanley Walker so she begrudgingly invited other high society people she mingled with occasionally. With dinner being over, people began to disperse, some leaving for the evening, others taking advantage of the open bar that Karen provided. The lawyer observed the people occupying the space of the ballroom, trying to figure out everyone's story from the way they interacted with others. He loved watching people and their mannerisms, the writer in him inspired by the events of people's actions and the words they say.  
  
He raised his glass to his lips, his eyes currently on an older couple who had their noses tilted up in a snooty manner when a quick movement from the corner of the room caught his eye. He frowned when he saw Jack whisper something in Karen's ear, seeing the smile grow on her face before they dashed out of the room. Will finished the last of his drink and went back to his people watching, shaking his head at his friends' erratic behavior. Minutes later, Grace came up beside him, her shiny golden dress sparkling in the light of the room and making Will wince slightly.  
  
"Can you believe this party?" she said in astonishment. "I've met so many awful, rich people who could be potential clients, its amazing. I'm drumming up business like crazy!"  
  
Will grinned at his roommate, rubbing her arm lovingly. "That's great, sweetie."  
  
"Where's Jack?" Grace asked, peering around the large room. "I saw him trying to flirt with an old guy earlier. He mentioned something about a sugar daddy."  
  
Will furrowed his brow, remembering his time a year ago when he unknowingly had a sugar daddy for about a week. "I'm not sure. He grabbed Karen a few minutes ago and they disappeared." It was then that he noticed they had actually been gone for quite some time as he checked his watch. "I'll go find them."  
  
"Hurry back," Grace said. "Mrs. Winston is coming this way and she has been throwing insults at me all night. I'll take it from Karen, but not from and old bag lady that smells like cough drops and moth balls."  
  
Will rolled his eyes and handed the redhead his empty champagne flute before he headed towards the hallway that Jack and Karen escaped to. He poked his head in a few doors, finding a bathroom, a linen closet, and a spare bedroom. When he came to end of the hall, he spotted one of the many libraries the manse had, the lights on and odd sounds leaking out of the cracked door. He stepped slowly into the room, turning his head one way and seeing a wall full of books. He was just about to open his mouth and call out their names when he turned his head the other way and saw two figures on the couch against the wall. An obnoxiously large string of mistletoe was hanging over the couch and Will quickly realized Jack probably lured Karen in there to take part in one of their innaprproate childish games.  
  
His eyes adjusted to the dimness of the room and his jaw dropped when he focused in on the couple occupying the library. Jack had Karen partially pushed against the arm of the couch, their bodies slanted almost diagonally along the cushions. The sound of their lips smacking together were loud even from where he was standing in the doorway. Their tongues visibly wrapped together before their mouths connected again in a series of kisses, Karen's hands on either side of Jack's face, holding him to her while Jack's hands were gripping her waist. He had a leg between hers, one foot on the ground to hold him upright as he stood over her, the other leg bent at the knee and digging into the cushion on the other side of Karen's hip.  
  
The lawyer felt like he couldn't move, his eyes locked on the sight of the raunchy pair, part of him piqued in interest, the other part disgusted. He watched Jack's hand that was on her waist as it smoothed up and down her side, fingers occasionally brushing the underside of her breast. Karen whined slightly in his mouth, her hips shifting around and Will could clearly see the whites of Jack's teeth as he smiled against her before Karen caught his upper lip between hers roughly. His hand that was caressing her side moved under her sweater, the other still wrapped around her back to keep her close. Karen whimpered when his palm flattened over her stomach and their mouths parted as they stared at each other through lust filled eyes. He pushed his hand inside the front of her pants and caught her gasp in his mouth, his tongue slipping back between her lips as he cupped her between her legs.  
  
Will's eyes felt like they were going to fall out of his head. He couldn't believe what he was seeing, never realizing that Jack and Karen's usually inappropriate games ever went this far. He still tried to rationalize in his mind that Jack wasn't really doing what it looked like he was doing, but the unmistakable movement of his hand and the way Karen was grinding her hips harder and harder into him told Will that they were definitely doing exactly what it looked like. His mind was racing, telling him to leave at once and to burn his retinas, but his feet refused to budge. He continued to watch on as Jack removed his lips from Karen's with a loud smack, his mouth trailing kisses down her jaw and neck as his hand moved faster between her legs. Karen's lips were parted as she took in rapid breaths, one of her hands falling to Jack's shoulder, gripping it tightly with her fingers. It was only when Will heard the sound of her high pitched keening did he finally find the energy to spin around and leave in a rush, wincing at the sound of a drawn out moan and a small shout of " _Oh Jack_!" following down the hallway.  



End file.
